Any web server software set up in 2000 and still running today unpatched could be pwned quickly. Including and especially NT 4.0. When you're running a server,

Any web server software set up in 2000 and still running today unpatched could be pwned quickly. Including and especially NT 4.0. When you're running a server, TLS is not the only service you are dependent on; you're also dependent on security updates. If they're not backported, you'll need to make version upgrades. Arguably it's better to think of every piece of software running on a server like it's a service, to maintain security and performance in an Internet full of hostile actors. I don't even understand the mindset of wanting to run a live server on ancient software, aside from doing it as a hobby. In which case, it's pretty typical for such hobbies to require extra work and care. Driving around in a car from 1940s takes more maintenance work, and is less safe, than a modern car, and everyone gets that.